


36

by FangirlOfTheCentury



Category: Supernatural
Genre: #Aufic, #CasHasBeenThroughIt, #DeanisaCompulsiveLiar, #Deanisdumb, #HurtComfort, #SetOutsideShowUniverse, #Strugglingloverstolovers, #slowburn, #slowburnkinda, ButHeWantsToFixIt, M/M
Language: English
Status: In-Progress
Published: 2021-03-19
Updated: 2021-03-26
Packaged: 2021-03-28 00:53:53
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 7,613
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/30131496
Author URL: https://archiveofourown.org/users/FangirlOfTheCentury/pseuds/FangirlOfTheCentury
Summary: Dean Winchester just wanted to be a different person for one day. For one coffee date he could be Michael Singer, a man who doesn’t have trauma, or depression, or a dick for a dad. Unfortunately one date turned into two years, and his current husband was not exactly thrilled to find out the truth.Based heavily off of the podcast musical written by Chris Littler, “36 Questions”
Relationships: Castiel/Dean Winchester
Comments: 2
Kudos: 12





	1. Let’s Play

Dean Winchester had built his life around a lie. For two years he lived under a fake name, with fake id’s and fake stories and a very very real husband. A husband who had disappeared into the night upon learning about Dean's faulty history, which in hindsight was a fair response. However,, in Dean's manic high of living the between life, he managed to find his sorry ass out of the empty bed at 4 am and on the interstate. At first he didn’t really know where he was going, but he figured his loving husband, Castiel, could not have gone much further than the good ol’ family cabin his parents owned that was roughly a 25 hour long drive from the apartment. It was fine. Dean deserved this.

He was pushing hour 8 of driving with no plans of stopping when the tire popped. He changed it in the rain. It was probably around hour 14 when he got sick of the music if that was even possible. He turned it down only for a minute to recognize that without music he was left alone with his thoughts. Quickly he cranked the shit out of it. Around hour 22, maybe because of the exhaustion or the desperation, or both, the cheesiest idea struck Dean like a stroke of genius. While pushing 85 down the highway he shoved his hand into the passenger glove box and dug around until he found it. A crumpled yet salvageable packet Cas had left there on their first date. This could be dumb enough to work. 

27 hours later and Dean was there. He felt nauseous and exhausted but deep down he wasn’t worried, not really. He had no reason to be! He had a plan, Cas loved him enough to marry him! I mean how different is a name! As Dean walked up to the door eyeing the parked truck in the driveway (just to make sure) he found himself knocking before he could think twice.

“Uh hey Cas, it’s your husband.” Silence. Dean paused waiting for a response, he didn’t get one. “Alright I know I deserve this, but I really want to talk to you alright? I mean I could keep talking to this door but the door isn’t nearly as sexy as you.” He let out a dry laugh. He had a feeling Cas was not amused, which almost made it funnier. “Okay so either you’re my husband, or you’re a complete stranger who’s squatting at my husbands house and if that’s the case I’ve got a shit ton of guns in my car.” He paused. “Or uh- unless I got the wrong house, in that case my bad. But I’m pretty sure this is Cas’s place” Silence again. Except for— what was that? Quacking? 

“I can hear you in there! At least I think it’s you, I don’t know I’ve never heard you make that sound before, but uh can you please let me in maybe? Or open the door? It would be pretty sad to drive 20 something hours to only get eaten alive.” Dean sounded a bit more desperate now, he had been talking for a few minutes and he wasn’t getting much back, but what can you expect when your husband thinks everything he knows about you is a lie? “Seriously, Cas please, you got me begging and you know I hate that shit. Can you please open the door, I really need to talk-“ he was cut off by the sound of the door swinging open, Dean nearly falls but keeps himself up when he sees his husband all scruffy faced and disheveled standing directly in front of him.

“I’m only entertaining this because I know you won’t shut up otherwise” Cas’s voice is deep and the words are sharp, but Dean can’t help but smile like an absolute lunatic as he finally _finally_ has a chance to get his perfect life back. Cas is looking at him expectantly, he looks tired and disappointed, but Dean knows he can fix it if he just pulls the right strings. 

“Cas, I know the last thing I deserve is your forgiveness, but I really want to explain myself, I really want you to get to know me.

You gotta understand I couldn’t just- I couldn’t just tell you everything-“ Cas was quick to cut Dean off.

“No I think you could’ve, because unlike you everyone else in the world decides to introduce themselves with a real name, and they don’t make up their entire past or they-“

“You’re not hung up on just the name are you? Because come on! Even if I’m not Michael I’m still me! There’s not much of a difference, you know the kind of person I am, you know what I like! You know what I hate, my favorite flavor of pie-“

“No _Dean_. It’s not just the name.” With that the conversation seemed to be cut short. If Dean was a smart man he would respect Cas’s space, he would leave now before making a fool of himself, but he was desperate and he wanted his husband to come back and realize it’s not really that big of a deal. The past was the past and they’re living now. Best to forget about all the gross shit and keep trucking forward, that’s all Dean ever wanted. After a moment of silence Dean breaks the tension.

“Is that a duck?” Cas is a bit put off by the question but nods _yes_ after a brief moment. He holds his finger up as if Dean would be going anywhere and shut the door between him and Dean. About a minute later he opened the door again and in his arms was a greenish brown duck, a _duck? Seriously?_ “Um-“

“His name is Crowley” Cas muttered looking down at the aquatic bird thing. Dean let out a snort as he held out his hand to pet him. Cas gave him a look of warning but Dean didn’t seem to notice, or if he did he didn’t care.

“You named your duck after a Good Omen’s character?” Dean just about scoffed, that was until the duck whipped his neck around threatening to bite Dean's finger off, for the first time since he got there Dean could’ve sworn he saw a small smile creep onto Cas’s face. Dean would’ve been pissed if he wasn’t elated to see Cas somewhat enjoy his presence.

“Maybe.” Cas said with a shrug as he gently ran his knuckle down the back of Crowley the duck, who didn’t seem as opposed to Cas like he did Dean. “The name kind of fit him though, he’s a bit of a trouble maker, but I found him quite literally lounging in my living room so I figured he could stay.” Dean was smiling now, he couldn’t help it, for a second things almost felt normal, with the exception of the break in ducks of course. 

“Hey uh- not to be that person but can I come in? The Mosquitos are kinda tearing me apart right now.” Dean let out a nervous laugh, he really didn’t expect he’d get this far, or if he did he figured it wouldn’t still be a big deal. He understood why Cas was upset, but abandon Dean in the middle of the night upset? That felt a bit drastic. Either way he was here now, and Cas no longer looked amused. After a good pause Cas stepped back and opened the door.

“Fine, but only because I know my consciousness will keep me awake if you get eaten alive.” Cas held the door open and Dean slipped in. The cabin was big but definitely run down. It was old, as it had gone untouched for far too many years, off the beaten path yet still owned by the Novak’s Dean was surprised it was just a duck who had taken residence. 

“You mean If I come in I won’t be eaten alive?” Dean shot him a teasing glance, and Cas faltered for a second. It’s hard when the man you loved three days ago effortlessly is now a known pathological liar and everything that you thought you knew might as well be dust thrown into the wind, Dean couldn’t imagine what Cas must be feeling right now. Rather than answer Cas just gives him a small smile only to look back seemingly much more interested with the broken light bulb and exposed wire then he is with his husband. “I brought all my documents, my fake ones I mean, the ones that say Michael Singer? I brought them thinking maybe you’d want to burn them- I mean we could burn em’ together, kill Michael together, and then maybe you can get to meet Dean?” Cas stiffened at Deans words. Poor guy looked as if a single poke would shatter him; he was so tense. 

“I didn’t come all the way out here to burn your papers, I didn’t come out here to befriend a duck, I came out here for one thing which was to get over you.” Yikes okay, at least he was being honest. Dean opened his mouth as if he could say anything that could defend his actions but quickly came up short. “I came up here for one thing, but now I have to change the broken light bulb, and patch up the leaky ceiling, oh and the toilets broken, the service is faulty, not to mention-“

“Hey let’s take it easy alright? You don’t gotta fix all this shit, not right now, and I know you’re probably doing it so you don’t have to worry about the bigger fish to fry, but speaking from experience I can promise long run? That don't work out too well.” The more Dean spoke the angrier Cas seemed to get. I mean sure he had every reason to be, but also Dean knew he could fix it. “Look maybe you don’t wanna kill Michael off yet, but I would like you to meet Dean? I uh I brought my passport.” Cas seemed to perk up at this. 

“And it has your real name on it?” He sounded genuinely curious, maybe a little bit hopeful, which Dean was eager to hold onto. Cas had his head tilted ever so slightly in question, Dean nodded. 

“Uh yeah, yeah it’s got my real name.” Dean led Cas to the old Impala and unlocked the passenger door. He reached into the glove box and pulled out a little dark blue booklet. He handed it off to Cas with a small smile and let take it. He watched, maybe a bit too eagerly, as Cas flipped it open. There he was, Dean Winchester, Born on January 24th, 1979 in Lawrence, Kansas. Cas’s brows furrowed as he traced his fingers over the lettering. 

“Kansas? I thought you were from Texas?” Cas looked up at Dean who once again was caught in his web of lies that had gotten them here in the first place. With a sheepish smile Dean looked at the picture over Cas’s shoulder.

“Yes and no, I spent a lot of time in Texas, but uh wasnt born there.” Cas was frowning again, he closed the passport and passed it to Dean. He looked as if he was gonna walk away, leaving Dean out here to get ax murdered or something, but the younger man was quick to stop that train of thought. “Uh wait, there’s one more thing” Avoiding Cas’s exasperated glare, Dean reached back into the Impala this time pulling out the old packet he had found earlier on his drive. He held the papers out to which Cas took them reluctantly. He let out a short scoff as he scanned the first words. 

“Oh my god you drove all the way out here so we could play 36 questions.” To say Cas looked annoyed would be a bit of an understatement. Honestly Dean should be used to it by now, but he knows his husband, and he knew if Cas really wanted him gone he wouldn’t still be here entertaining this charade, and that was pretty promising on its own.

“Aw now tell me you didn’t forget! These aren’t just 36 questions, these are the-“

“36 questions that lead to love, yes how could I forget our first date.” Cas finished in a dry tone. Dean was smiling though, he knew this was serious, this whole situation was very serious. But something about the terrifying reality of having to tell the complete and utter truth to your husband you have been lying to for two years felt absolutely historical. 

“That’s the one.” Dean added with a smirk. “I think we should play. Right here right now.” Cas shook his head as if he had already made up his mind. “No seriously, we can play and I will answer with complete honesty. I owe you that much.” Dean could tell Cas was breaking, his eyes kept catching Dean’s. He was intrigued. 

“Complete honesty?” 

“Complete honesty.” Cas was hesitant, but nodded at Deans last statement. Dean let out a breath he didn’t know he was holding and held up the paper to read. “You remember how the game works, I’ll ask the odd questions, you ask the even.” Dean took a deep breath. “Okay. Question 1.”


	2. Questions 1-5

They were interrupted by a loud clap of thunder. Dean recalls the sky being a somewhat dreary sight on his drive up, but now it was much much darker. He was so enthralled with the task at hand that neither of them noticed that the sky had turned a dark grey, and the winds that had started to pick up. A single heavy drop fell onto Dean’s hand, then there were two, then three, and before Cas could open his mouth the boys were caught in a downpour. For the first time since Dean arrived, Cas was laughing, seriously laughing! Dean was laughing too, though something told him Cas was much more enthusiastic.

“So we're gonna go in or are you gonna stand in the rain forever?” Dean yelled over the wind and rain, to which Cas just shook his head. He didn’t say much else, but rather motioned Dean to follow as he ran towards the front door. 2 minutes later and the boys were inside, completely drenched, and out of breath. For a second Dean could swear Cas was not just looking at Dean, but _looking_ at Dean. “Not for nothing Cas, but the last time you looked at me like that? Well let’s just say I had a hard time walking the next day.” Cas looked up, eyes wide, as if he was a kid who got caught with his hand in the cookie jar.

“What? No! No I wasn’t looking at you like _that_. No. No, I was just lost in thought.” Cas looked away, his face was flushed and it took a lot of Dean not to comment just how cute he was being. Man was a fucking beast in the sheets, but the sheepiest nerd in the world any other time of day. “Let’s uh, let’s just get this over with. You were about to ask the first question?” Dean nodded, and pulled the now slightly damp papers out of his jacket and read off the first line.

“Question 1. If you could have dinner with anyone in the world, dead or alive, who would it be?” Dean looked up at Cas expectantly, he had an idea of who he would say but he would like to hear it from him. However the more Cas seemed to squirm the less Dean was sure.

“Uh, Michelle Obama.” Dean raised a brow at Cas’s words. Yeah no. He didn’t buy that for a second.

“If this is going to work you gotta answer honestly.” Dean sighed with a shrug, crossing his arms over his chest. Another moment passes and Cas shakes his head. He turned his back to Dean and suddenly let out an exasperated yell. Crowley the duck also let out a shriek purely to be a nuisance. Cas whips his head back around and looked the other in the eye.

“If I could have dinner with anyone in the world, dead or alive it would be Dean.” His voice was gruff as he continued to speak. “I could have dinner with Gandhi, or Da Vinci, or Oprah, but if I had to choose, I would throw it all away to have dinner with Dean. Dean who I had never met, or thought I knew, just Dean Winchester. I would have dinner with you.” Dean couldn’t help but smile at that, how could he not? Cas wanted to have dinner with him! Okay maybe under different circumstances but hey he’d take it. “There, okay I answered the question, let's move on to the next one.” Cas was avoiding his glance again, almost embarrassed by his honesty. Dean shook his head.

“Hold on I didn’t get to answer.” Cas looked up for a brief moment, Dean was staring at him with a childish expression. “I bet you could guess who I would pick?”

“Yes, I probably could,” Cas grumbled, taking a moment to look over at Crowley, who was most definitely judging Cas right now. Dean was still staring at him expectantly, as if he wanted Cas to indulge him, and play the game. “Dean-“

“It’s you, ya son of a bitch.” Cas rolled his eyes. Dean always had a habit of stating the complete and utter obvious, that’s one of the first things Cas fell in love with, as annoying as it was. Well except, it wasn’t Dean, it was Michael. Dean was still staring at him, half expecting him to laugh or grunt or something but Cas was giving him very little. “You uh- you wanna ask the second question?” Sure Dean was a little on edge, but honestly he was just impressed he got this far. Cas opened his mouth as if he were going to say something, but opted to stay quiet as he wordlessly took the packet from the other’s hand. 

“Question 2. If you had the ability to be famous would you? If so, what would you be famous for.” Dean let out a soft scoff, and shook his head. 

“Nah.” Cas tilted his head at him, and Dean simply shrugged. “I wouldn’t wanna be famous.”

“Why?” Cas prodded, probably a bit more accusatory then he meant it to be.

“That’s not the question is it.” Dean shot back. Cas let out an annoyed sigh, it was probably the 5th time he’s made this noise within the hour and Dean woulda called him on it too if he wasn’t interrupted by another loud clap of thunder. 

“I’m gonna go get a drink, you still take whisky?” Dean hummed in assurance to Cas’s question, only to point an accusatory finger a moment later.

“You didn’t answer the question.” Cas glanced down, a small smile crept onto his face. He looked back up to meet Dean’s eyes and passed him the papers.

“Yeah, yeah I would. If I could be famous, I would want to be known for creating a giant cross country scavenger hunt that raised money for all kinds of charity organizations, weirdly specific but I think that’s why I like it.” He paused, “I also think I could crush in Survivor.” Dean watched Cas for a second, smiling even as Cas disappeared into the other room. A few minutes later, Cas returned with a single bottle of unopened whisky. He placed it on the table and unscrewed the cap. He plopped down on the old leather couch next to Dean. “I couldn’t find any glasses, well none that looked sanitary, but I figured the bottle would do.” Dean grinned, reaching over to take the bottle off the table before Cas could even get the cap off.

“Don’t mind if I do.” Dean brought the glass bottle to his lips and chose to ignore Cas’s disappointed glare. When he put the bottle down he caught Cas staring at him, it wasn’t a cute doe eyed far off look, no it was quizzical and hesitant, and it hurt Dean so to avoid that feeling he took another drink. “Alright question 3 is me.” Dean cleared his throat, and pointed to the third question on the list. “Do you rehearse phone calls before you make them?” Cas paused for a second, and then took the bottle from the table and nodded. 

“Oftentimes yes. You knew that though.” Cas sighed, twisting open the cap. Dean simply shrugged.

“I know, but we’re making this an authentic experience.” Dean let out a short chuckle of sorts “and in this case I’m sure you know that I am very much balls to the wall. If shit comes out shit comes out.”Cas let out a low hum as he practically cradled the whisky bottle. 

“I’m sorry, but Michael-“ Cas was quickly cut off by Dean.

“Dean.” Cas physically cringed at the slip up. His nails pushed into the label of the whisky bottle and he averted his gaze only for a moment.

“ _Dean._ I’m sorry, but I’m still trying to process this. I mean I can’t even get your name right, I feel like I don’t know you at all.” Cas muttered, but Dean quickly shook his head. He moved closer to Cas, not so close that they were touching, but close enough.

“I know you feel like everything I told you was a lie, but you know more shit about me than anyone else I know.” Dean paused for a second, pursing his lips. “Alright uh, me and Michael? We both have the same taste in music? Led Zepplin all the fucking way” Cas almost smiled at that, Dean took it as an invitation to keep going. “Me and Michael both love the shit out of a good Apple pie, we both have the same amount of love for the old car parked out front.” He paused “same taste in guys that’s for damn sure” Cas rolled his eyes, but now he was looking at Dean. “I want you to know everything, not because it’s fun for me, actually if I had the choice I’d rather stick a knife in my eye, but I want to do this for you.” Dean didn’t like how raw he sounded, he hated that this whole exercise was based around his vulnerability. “But uh, I gotta work up to that, so at this point let’s just get to question 4.” Cas was always an amazing listener, every time you spoke to him you just knew he’d take in every word. Dean admired how easy Cas could drink it all in, and the patience he could have in any given moment, especially in times where Dean felt a bit more sporadic. That quality would especially come in handy in a super common situation like this. 

“Yeah. Okay question 4.” Cas took a deep breath, almost like he was composing himself, and leaned over the paper. “If you had to describe your perfect day, what would it look like.” Cas realized he was still holding onto the whisky bottle, and sheepishly put it back down. Dean watched as Cas’s head turned to the duck that was now sleeping peacefully on the old rocker across the room. And Dean watched as Cas walked his cute ass over there, grabbed the duck off the seat and came back. Dean raised a brow. “What? He looked lonely.” Dean still hesitated, watching Cas and his pet with the utmost amusement. “Dean, you’re stalling.” Cas just about grumbled, running his knuckle down the ducks neck.Crowley was no longer asleep, and Dean could swear the duck was staring daggers into his soul. 

“Well I’m pretty sure I’m gonna be hate crimed by your duck, so uh sorry if I’m a little taken aback.” Dean chuckled at his own joke, and Cas scoffed. It was an endearing scoff though, Dean had been able to tell the difference only 6 months into dating Cas. It would've been shorter if Cas wasn’t so muted with his emotions, and it would’ve been longer if Dean didn’t have a history with women. “Alright, I guess my perfect day would definitely involve my baby.” He shot a quick glance out the window to make sure the Impala was still in good shape. “And loud classic rock. Pie is a must, and uh yeah just go where the winds took us.” Cas didn’t look impressed.

“That’s what you said the first time.” Cas was watching Dean now, as if he was studying him. Dean sighed rubbing his fore finger, and thumb in between his brows. 

“Yeah uh, it is.” Cas gestured to him to keep going. “I mean not much has changed, but being completely honest, no shits and giggles, I have learned that you gotta live every day as if it was the perfect day.” Cas’s face had softened. “I know that’s the cheesiest thing I’ve ever said, but uh you never know what the day could bring, and tomorrow always has the possibility of being better than today.” Cas looked like he was about to take Dean's hand, but like the impeccable timing they had, both boys jumped when a large crash came from outside. The rain was coming down harder, and now the trees appeared to be toppling over as well. “Jesus Christ.” Dean muttered under his breath. “Uh here you go so I can focus on that and not the fear that my car could be crushed at any minute.” 

“Well you know my perfect day.” Cas began, but Dean shrugged, encouraging him to continue. “While I agree with everything you said, if I had to be original and choose my perfect day it would be one where I could all my time outdoors. Nothing too extravagant, but just a relaxing picnic where I could listen to the bees, and drink expensive champagne.” Cas’s voice had sort of trailed off, he’d be lying if he wasn’t referring to one of the earlier dates Dean had taken him on. When they first played, Cas answered this question fairly similar, and Dean listened. For their half year anniversary, Dean or Michael had given Cas his perfect date. Dean also picked up on this, he looked away, ashamed. Because how could he forget? Things were so easy back then. But it didn’t have to be a somber memory! The relationship wasn’t over and Dean was sure he could salvage it. 

“A man of simple taste doesn’t change much does he.” Dean smiled, it was meant to come off as a joke, but something in his tone read a bit more somber. Cas noticed this too, but he just nodded rather than address it. Time would heal all wounds, at least that what Dean had hoped. The younger man cleared his throat, choosing to continue the game rather than address the unspoken tension. “Question 5 when was the last time you sang, to yourself and to someone else.” Cas actually cracked a smile for this one. 

“Well I don’t really sing, but the last time I sang to myself was when I was stress fixing the bathroom sink this morning, and the last time I sang for someone was when I wanted Crowley to eat his cut up strawberries.” Dean laughed, like really laughed, probably a bit louder then he should’ve, but what can he say? He wasn’t expecting that at all. 

“Your duck doesn’t count!” Dean grinned, shaking his head as Cas’s eyes went wide and accusatory. 

“Yes it does! He’s not me and I was singing to him about strawberries! I think that counts.” Cas was laughing now too, and for a second things felt normal. “Now please go before you make me sing the strawberry song for you too.” Dean shook his head, still giggling at Cas’s words. He put his arms up in defeat, to which Cas grinned at. 

“Okay okay, the last time I sang to myself? Was definitely on the way up here, it’s the only way I could keep myself awake, and in front of people? Jesus I don’t know, I mean I know you hear me sing all the time but the last time I purposely sang for someone I think was at that roadhouse bar when I got trashed and sang Good ol’ boys a few months back.” Dean chuckled and grabbed the whisky, deciding it's been far too long since he last had a drink. 

“Oh how could I forget, I think I still have that on video somewhere.” Cas hummed, he looked over at Dean and took the bottle from his hands, then proceeded to almost drop it as another crash from a fallen tree echoed through the old cabin. Luckily he kept his grip, but the flickering lights that was followers by complete darkness couldnt exactly have been avoided.

“Shit.”

**Notes for the Chapter:**

> I’m gonna try and post every Friday, but for now here’s chapter 2!!


	3. Questions 6-11

**Summary for the Chapter:**

> The questions continue, and Cas finally starts to understand who Dean really is.

“I can’t believe you made us leave the cabin.” Cas shot a glance at Dean before promptly looking out the Impala window. The rain was still coming down hard, but rather than staying safe and bundled up inside the established building, Dean decided that it would be best if they abandoned the cabin in an attempt to maybe find a place with working power, and running water. 

“I didn’t want a tree fallin on baby.” Dean was yelling over the music that was promptly being blasted through the speakers. Cas let out an exasperated sigh and reached over twisting the dial to turn it down. Dean let out a mock gasp of terror to which Cas rolled his eyes. “Ey you can’t do that to Jovi!” Dean proclaimed, he reached out to turn the dial back up, but Cas slapped his hand away. Dean took his eyes off the road to glare at his almost ex husband. “Come on man!” The duck, that Cas insisted on bringing, seemed to squawk in agreement.

“Dean this is serious, what is the plan anyways. Where are we going?” Cas muttered, he turned his head to glance over his shoulder to make sure Crowley was okay, still tucked away in his little blanket nest. Next to the duck, was the half drunk bottle of whisky that Dean had encouraged, which he knew would come in handy right about now seeing as Cas reached his arm behind him to grab that exact bottle. He untwisted the cap and took a long unpresidented swig. 

“Woah there cowboy. I know you like to show off your tolerance, but why don’t we slow it down.” Dean could’ve sworn he heard Cas mumble something in his defense, but he didn’t quite catch it, so Dean decided to skate by it. “Also I passed a few motels on the way here, I was thinking we could stay there.” Dean could practically feel Cas’s look of warning. Dean just smirked. “It’s gonna be a bit til we get there though. Why don’t we keep playing? Uh here I know it’s my question but being the responsible driver I am why don’t you say it and then you’ll answer first.” Cas tilted his head at Dean, opening his mouth in protest, but Dean didn’t give him the chance and pulled the papers out of his jacket shoving them at Cas. 

“Fine.” Cas sighed begrudgingly “if you were 90, but had the choice to retain the mind or body of a 30 year old what would you choose.” Cas let out a quiet scoff “I would choose mind. There’s something about the uh value of the mind and being smart” Cas was slurring, just a little bit. It was kind of cute, and a little worrisome, but Dean wasn’t gonna focus on it too much. “What about you  _ Dean.” _

“Oh body of course.” Dean stated pretty quickly, which Cas responded with a snort. “Don’t make fun of me! When we’re old one of us has to be the hot one. You can take care of me, and I will keep up the appearance.” Dean rambled a bit, trailing off in the end almost afraid of what Cas was going to respond to that with. But when Dean looked over at him he was giggling. Smiling with his head pressed back against the seat. 

“God this is so absurd.” Cas chuckled breathlessly, “I can’t believe I agreed to this, I can’t believe any of this is happening.” Dean raised a brow, but didn’t interrupt him. “And I can’t believe i'm entertaining this, and I’m gonna keep entertaining which feels even crazier.” Cas shook his head as he fiddled with the papers. “Question uh, question 7.” His smile faded “do you have a secret hunch about how you’re going to die.” He looked over at Dean “why do I have a feeling this question isn’t going to match Michaels.” 

Dean bit his cheek, he didn’t meet Cas’s gaze, and his fingers tightened around the wheel. “Uh yes and no.” He muttered. “When I first answered the question I said didn’t have a hunch, just an acceptance to it. I’ll let it come when it comes ya know.” Cas hesitated for a second, but then he nodded. “Well I guess that’s still true, but I also had a hunch for a long time that I would die alone. I still kinda do, it’s a big fear of mine.” Cas was watching him with an intensity now, and Dean thought he was gonna shatter under the weight of his stare. “Uh sorry, was that too deep?” Dean uttered a bit sheepishly. 

“No, no it was honest.” Cas whispered. “And honesty is good.” Dean just nodded at that, unsure how to respond. He wasn’t kidding when he said he’d rather take a knife to the eye then admit that he’s not as put together as he’d like to appear. But if this is what wins his husband back, he’s willing to try. “Alright uh, if I had a hunch about how I was going I would say.” Cas hesitated, starting to smile again. “God knowing my clumsy ass id probably slip in the shower and that would be that.” Dean couldn’t help the audible laugh that came up from his chest. Cas tried to look offended, but he couldn’t help but laugh as well. “What! Why are you laughing at me.” 

“It’s just, it’s so accurate. You are the clumsiest son of a bitch I know.” Dean giggled, wow Cas was actually sorta warming up to this. He looked more relaxed, and maybe it was just the booze, but Dean was sure this was working, despite how torturous some of these questions were going to be. The rain however seemed to be coming down harder than it was before, if that was possible. “Shit, I can’t really see, uh it’s fine! It’s fine I’ll pull into this gas station and we can continue the questions.” Dean took a grip on the wheel and turned it probably a bit sharper than was necessary, Cas grabbed the handle above the door in an “oh shit!” panic

“Was that necessary?” Cas just about spat, to which Dean just shrugged with a shit eating grin plastered on his face. 

“Of course it is Angel.” God why was Cas so perfect, his face was flushed, and he was all flustered again just like he was when they first started dating. Everything about him was too good for Dean. Ignoring the sinking pit in his stomach, Dean put the car in park and pulled up the questions. “Name three things you, and your partner have in common.” Dean looked up at Cas “easy, we both love westerns, we both suck at cooking, and we both get way to competitive when we do game nights.” Cas hummed low in agreement. He took another drink of the whisky and passed it off to Dean. 

“First of all, I don’t love westerns. I just appreciate them, and second of all, three things? Alright we both think children shouldn’t be allowed at weddings, we both really really hate spiders, and we both sleep better when it’s raining.” Cas’s eyes were trained on Deans, his voice getting softer as he kept listing off their similarities. Dean would be lying if he said his heart wasn’t beating out of his chest. Cas cleaned his throat, rather than address the tension in the room, or car, he read off the next question. “Question 9, what in life are you most grateful for?” Dean paused, thinking about it for a second. 

“I’m grateful for stability, it’s not something I had most of my life, but when I do feel like I can stand on my own two feet and not fall over, it’s nice.” Cas didn’t seem to respond to that, he looked as though he was deep in thought. After a moment he nodded, assuring Dean he was listening. 

“That’s understandable.” Dean was grateful he didn’t push, he could’ve, he had every right to, but Cas knew he would tell him more when it was time. “For me, I am most grateful for-for honesty.” Cas looked away, avoiding Dean's eyes. “If we’re being completely honest.” He added under his breath. 

“No, no yeah honesty is good. Even if it is a bit of a call out, I deserved that.” Dean uttered, what else could he say? He didn’t exactly have the right to be on the defense here. “Hey uh, I think we switched? Game plan was I ask odd you ask even, so for continuity sake why don’t you just ask me the next one too.”

“Okay. Alright sure, question 10, if you could change anything about the way you were raised what would it be? And why.” The more Cas spoke, the more Dean regretted passing this question onto him. He looked out the window, a dry laugh escaping his throat.

“Is it safe to say everything.” Dean sighed, Cas raised an eyebrow expecting more. 

“Well last time you said you wished your parents were alive, has that changed?” As the words came out of his mouth, Cas stopped. His eyes widened as he looked at Dean with a new found anger. “Are your parents alive? Did you lie about that too?” Dean opened his mouth in protest, but quickly closed it because what could he say.

“I-yes. Yes, and no.” Cas through his hands up, but Dean quickly tried to back track. “My, my dads alive. I didn’t lie about the house fire, but the outcome is different.” Dean was speaking sort of fast, but at least Cas was listening to him now, even if it was begrudgingly. “When I was 5, my house caught on fire. And my mom did pass away in that fire, but my dad got out, me, my dad, and my brother.” He hesitated watching for Cas’s response.

“You have a brother?” Cas sounded hurt more than anything.

“Yes, yeah yes and we used to be super close, mostly because my dads a complete dick.” Dean huffed with a forced laugh. Cas didn’t say anything, so Dean kept talking. “When my mom died, he was convinced the fire was not an accident. I mean my dad was really sick, he wasn’t all there, so when the statement came up that the house fire had an “unknown cause” he was convinced it was on purpose, and we- we traveled the country looking for whoever started this house fire.” Dean let out a shaky breath “of course we never found anything, it was a freak accident not a fucking arrsonist, and it’s not like I could tell him that. Though I tried.” He trailed off. “Uh long story short, he wasn’t a good guy, he didn’t approve of me, and if he ever found out about you he’d disown me anyways so I figured best spare you from that shit show.” Dean let out a shuddered sigh, a nervous laugh escaped his throat “I uh, I haven’t thought about that stuff in a long time.”

“What about your brother?” Cas’s voice was soft.

“Oh uh, yeah. Well he went to college, he got out, I didn’t. I stayed here, and one day it got unbearable and I found myself way too drunk out where I shouldn’t have been. I’ll spare you the details, but let’s just say I stood on that bridge for a long time, before I eventually came down, after that I decided my brother could never know, so I ran.” Cas looked so pale, Dean tried to give him a reassuring smile. “Hey I’m okay now! That’s all that matters, but uh Sammy eventually found me, I mean he was the one who went looking for me, not my dad. I’m pretty sure he’s the one who sent those two guys at our door asking for Dean Winchester.”

“Dean I-I didn’t know I’m so sorry.” Cas whispered, but Dean just waved his hand as if it were nothing. 

“Nah it’s okay, my past was shit but it’s gotten much better.” He paused “what about you? Anything you wish you could change.” Cas hesitated for a moment, reflecting on what Dean had asked. 

“I guess, I would ask my mother to raise me to be a little more independent.” He sighed. Dean snorted and playfully shoved his arm. 

“As if you could ask your mom to raise you differently.” Dean snorted, to which Cas smiled ever so slightly. “Well in order to keep the game moving, I will ask you question 11, in four minutes. Tell me your life story.” Cas still looked taken aback, but seemed to come back to himself when Crowley the duck made his appearance once more, because of course he would.

“I don’t think we need to, I mean you already know my life story.” Cas sighed, leaning his head back against the window. Almost as if he was studying the rain that was trickling down the window. Dean held back a comment about the droplets racing, maybe it wasn’t the time. 

“I do, but I’d like to hear it again.” Dean whispered. Cas sighed, he lifted his head up and cleared his throat. 

“Well I’m sure you won’t have time for me, but basically I was born in Phoenix Arizona, I lived in a super Christian household, my dad left my mom and I when I was 7. When I came out to my mom she was surprisingly supportive , uh I had my first boyfriend at 16, Zack McClain, lost my virginity, got broken up with.” He took a breath, then continued. “Uh then I went to college, focused on my studies, missed out on a lot of the college experience, got my teaching degree, moved to Seattle, went back to school to further my degree, and then uh, then I met you. We got married even though most people said it was too soon, and uh now we’re here.” He paused glancing down at his lap. “And I had to tell my mom she was right.” Cas let out a dry laugh. “And I hated that she was right.” Cas shook his head, and glanced up at Dean. “Now you.”

“Alright my turn, well okay you know my mom died when I was five, my dad took me and my brother all over the country looking for a non existent murdere. Then I fell a little off the rails, got into a big blow out fight with my brother who told me to never speak to him again, uh almost through myself off a bridge, stole my dads car and then I ended up in Seattle, and that’s when I met-“

“Hold on your moving way too fast” Cas sounded a bit frustrated but Dean held his hands up in defense. 

“I want to tell my life story in as much detail as possible.” Dean shot Cas a glare which stopped whatever protesting he was gonna do. “When I was in Seattle, I came across this guy, sitting alone at a coffee shop, and he looked all shy and charming, and so I went over and I sat next to him.” Cas’s face softened “and I asked him if he had any good coffee recommendations, and I swear he was gonna just blow me off, I mean I get it I’m a jackass.” Dean kinda smiled at that, so did Cas. “Then after a moment, he told me if he had to choose, he would rather drink tea, and then that his name was Cas.” There was a pause “and when he asked my name, I heard the perfect opportunity. I didn’t have to be this guy, I didn’t have to have this fucked up past, I could be Michael and I could have the life I always wanted and we didn’t have to focus on any of the bad shit.” Dean looked up at Cas, and he let his guard down. “I got the life I always wanted with you, I finally understood what love could be, and it was always okay with you. Cas when I was with you I was more myself than any other time in my life, but I shouldn’t have dragged you along and I’m so sor-“ He was cut off. Cas’s lips were on his and Dean felt as if he was flying. The kiss was eager and warm and angry and sad, and everything Dean missed about Cas. When Cas had finally pulled away. They were both panting, and then they were laughing. “I uh, happen to know were about 2 miles from a motel.”

**Author's Note:**

> Schedule wise I’m hoping to knock out a chapter each week, but overall I have my shit organized and I hope you guys plot this idea as much as I do. 
> 
> Also seriously check out 36 questions, it’s really really cool.


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